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Added 3 mins ago
Senior Internal Auditor
Co-operators
Guelph, ON · Burlington, ON · Regina, SK
Full-time
As the Senior Internal Auditor, you will independently lead operational and advisory engagements from planning through reporting. The Senior Internal Auditor will develop risk-based audit…
Added 3 mins ago
Project Manager
ENMAX
Calgary, AB · ENMAX Place, Calgary, AB
Full-time
We are looking for a Project Manager to lead projects and programs that help deliver ENMAX Power’s capital plan. You’ll bring people together, keep work moving forward and help ensure…
Added 3 mins ago
Junk Removal Specialist
1-800-GOT-JUNK?
Calgary, AB
Southwind encourages team members to lead with innovation and purpose. We're a company built on integrity, teamwork, and ongoing development. Join us and help redefine home services. Apply…
Added 3 mins ago
Relationship Manager, Commercial Financial Services - Indigenous Banking
Royal Bank of Canada
Ottawa, ON
Full-time
…businesses. This individual will also be working with a broader team of bankers supporting Indigenous Commercial Banking. This team will focus on providing tailored financial solutions,…
Added 3 mins ago
Revenue Operations Manager
Lightspeed Commerce, Inc.
Remote, Canada
Full-time · Remote
The Revenue Operations team is central to the success of our go-to-market functions. As the Manager of Revenue Operations for the B2B business unit, you will build and lead a…
Added 3 mins ago
Housing Focused Shelter Team Lead
The Mustard SEED Society
Saskatoon, SK
Full-time
The Shelter Team Lead fulfills the mission of The Mustard Seed by maintaining a high level of professionalism and respect for all who enter the space and live in the neighborhood. Reporting…
Added 3 mins ago
Growth Marketing Manager
Alternative Payments
Remote, Canada
Full-time · Remote
We're growing fast, thinking big, and building a global team that wants to be part of something that lasts. We believe the best solutions come from diverse perspectives, deep collaboration,…
Added 3 mins ago
Senior Product Manager - Developer Productivity
Okta
Toronto, ON
…getting outsized results and turn their patterns into playbooks; lead build, buy, integrate, and standardize decisions, including the vision for reducing implementation diversity across…
Added 3 mins ago
General Labourer - Desserts
''
Florenceville-Bristol, NB
Full-time
Relay information to other Team members as an area Lead (Key Area Resource).
Added 3 mins ago
Director, Commercial Finance Agriculture
Royal Bank of Canada
Guelph, ON
Full-time
As Director, Commercial Finance, you are part of a team of client-facing credit professionals aligned to our Large Agriculture client segment. You play a key role in realizing our business…
Added 3 mins ago
Senior Customer Success Manager
Staffbase
Canada
$100,000 to $110,000 CAD / year
…Sydney, Tokyo, Prague, and Minneapolis–St. Paul, our diverse team of 550+ employees supports 1,500+ customers - reaching over 14 million employees - in transforming their employee…
Added 3 mins ago
Senior Customer Success Manager
Staffbase
Toronto, ON
$100,000 to $110,000 CAD / year
…Sydney, Tokyo, Prague, and Minneapolis–St. Paul, our diverse team of 550+ employees supports 1,500+ customers - reaching over 14 million employees - in transforming their employee…
Added 3 mins ago
Geotechnical Driller
Acuren Inspection, Inc.
Calgary, AB · Three Hills, AB · Edmonton, AB · Grande Prairie, AB · Lethbridge, AB
Full-time
Acuren Wind is looking for an experienced Geotechnical Driller to join our growing team in Calgary, Alberta.
Added 15 mins ago
Queen’s National Scholar (QNS) Assistant Profes...
AI Venture Studio
Kingston, ON
Full-time
Added 15 mins ago
Retail District Manager - Canada West
adidas
Vancouver, BC
Full-time
The successful candidate will have a strong growth mentality, a passion for sport and retail, and the ability to lead through influence, accountability and collaboration. They will balance…
Added 15 mins ago
Bus Operations Support Lead I
TD
Calgary, AB
Full-time
May act as a team lead, coordinating the work of others and providing coaching to maintain service, process and product standards
Added 15 mins ago
Desktop Support Analyst
Saskatchewan Polytechnic Alumni
Prince Albert, SK
Full-time
Reporting to the Endpoint Compute & Desktop Services Manager, under the mentorship of the Team Lead, the Desktop Support Analyst role is to provide a single point of contact for end users…
Added 15 mins ago
Key Account Supply Chain Manager - TORONTO
L'Oréal
Toronto, ON
Full-time
A Day in the Life Reporting to the Supply Chain Director, you will lead the strategic collaboration with our major retail partners (Loblaws and Shoppers Drug Mart), managing a dedicated…
Added 15 mins ago
Principal Process Automation Engineer
Worley
Vancouver, BC
Full-time
Work with Worley offices to share work and integrate staff on projects for a blended execution team.
Added 15 mins ago
Maintenance Manager
TalentSphere Staffing Solutions
Saskatoon, SK
Full-time
…helping develop the overall technical strength of the maintenance…
Added 15 mins ago
Yard Associate
Kent Building Supplies
Gander, NL
Part-time
…Ontario, Newfoundland and Labrador), as well as in USA. We are a team of 20,000 dedicated employees. At J.D. Irving, Limited, you are part of a dynamic team of professionals who lead with…
Added 15 mins ago
Avionics & Communication - IPT Head
Apptoza Inc.
Montreal, QC
Contract
Lead the Avionics & Communication Integrated Product Team (IPT) and ensure alignment with overall aircraft program objectives.
Added 15 mins ago
Chief Financial Officer (CFO) Strategic Business Executive
Grey Eagle Resort & Casino
Calgary, AB
Full-time
…principal financial advisor to the Board and Executive Leadership Team, providing leadership across financial operations, capital investment planning, enterprise risk management, business…
Added 15 mins ago
Project Analyst II
TD
Toronto, ON
Full-time
May lead and deliver Tier 5 projects with a low level of regulatory oversight, risk and complexity profile with medium term horizon
Added 15 mins ago
Senior Internal Auditor
Co-operators
Burlington, ON
Full-time
As the Senior Internal Auditor, you will independently lead operational and advisory engagements from planning through reporting. The Senior Internal Auditor will develop risk-based audit…

Sentry

Senior Technical Support Engineer

Remote, Canada

Pay: $125,000 to $150,000 USD / year
Job type: Full-time
Workplace: Remote
Experience: 5–8+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
Posting language: English
Posted: Sep 30, 2026

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Original job description

About Sentry

Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building.

Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future.

About the Role

At Sentry, Support is an engineering discipline. Our customers are the greatest technical minds in the world - developers at elite enterprises building the future of software - and they deserve answers that go deeper than a knowledge base link.

We are architecting the Technical Support engine. We’re looking for a veteran engineer to help us redefine the standard of technical support by combining deep human expertise with autonomous agentic systems. You are a debugger of both code and systems. You will treat support volume as a data signal to build automated resolution paths, ensuring our human engineers only touch the most complex, high-impact architectural puzzles.

Sentry Support Engineers aren't just clearing queues; they are Orchestrators. You will engage with our users across GitHub, Discord, and our internal systems, while acting as the Technical Lead for our Agentic Ops. You ensure that when a developer asks a complex question, our systems have the right context and a seamless "Human-in-the-Loop" path to you when deep, nuanced expertise is required.

In this role you will

Master the Sentry Ecosystem & Support Elite Developers

Deep-Dive Debugging: Perform root-cause analysis on complex issues and distributed tracing gaps across polyglot environments.
Support the Great Minds: Act as a strategic consultant for senior engineers at our largest enterprise customers, solving high-stakes architectural challenges that push the boundaries of observability.
Troubleshoot SDK Implementations: Go deep into the source code of Sentry’s SDKs to help developers instrument complex frameworks and custom environments.
Engineering Feedback Loop: Serve as the bridge between the world's best developers and our product teams, using data from your systems to prioritize high-impact platform fixes.

Engineer Agentic Operations (The Scaling Engine)

Deterministic Support Paths: Engineer the logic that powers our support agents, moving beyond probabilistic guesses to high-fidelity, autonomous resolutions.
Knowledge Engineering: Build the right context into our systems so they can resolve issues consistently and indefinitely.
Agentic Tooling Development: Use MCP (Model Context Protocol) and Sentry’s internal APIs to build "skills" for our agents, allowing them to perform complex lookups or state-checks autonomously.
The Seer Philosophy: We’ve already proven AI can handle autonomous production fixes with Seer. You will apply that same philosophy to the support lifecycle - moving us from a "Help Desk" to an "Autonomous Resolution Engine."

You’ll love this job if

You love eliminating Non-scalable effort: you enjoy automating repetitive work and take pride in building systems that save time and effort.
You’re a Full-Stack Troubleshooter: You enjoy jumping from a React frontend issue to a Python backend trace to a CI/CD pipeline failure in a single afternoon
You Value Evidence-Based Support: You prefer looking at data trends over anecdotal evidence to decide where to build automation next.
You’re a Developer Advocate: You want to guide the industry on how elite engineers and AI co-exist in a high-density technical ecosystem.

Qualifications

5–8+ years of experience in technical support engineering, systems engineering, or software development, with a track record of solving high-complexity SaaS problems.
Strong Coding Foundations: Mastery of Python, JavaScript, Java, or Ruby. You are comfortable reading SDK source code and identifying bugs in production-level repositories.
Systems Depth: Deep understanding of distributed systems, microservices, APIs, and the "path of a pixel" from frontend to database.
AI & Automation Literacy: Practical familiarity with LLM orchestration (RAG, context windows, system prompts) and a critical eye for where AI succeeds versus where it requires human intervention.
Exceptional Communication: The ability to explain complex architectural concepts to a human and write precise "system instructions" for an AI.

Bonus qualifications

Open Source Contributor: An active presence on GitHub or experience maintaining open-source libraries.
Former Software Developer: You’ve spent time in the trenches as a full-time dev and know exactly what keeps our customers up at night.

The base salary range (or hourly wage range, if applicable) that Sentry reasonably expects to pay for this position is $125,000 to $150,000. A successful candidate’s actual base salary (or hourly wage) amount will be determined by a variety of relevant factors including, without limitation, the candidate’s work location, education, work and other relevant experience, skills, and job-related knowledge. A successful candidate will be eligible to participate in Sentry’s employee benefit plans/programs applicable to the candidate’s position (including incentive compensation, equity grants, paid time off, and group health insurance coverage). See Sentry Benefits for more details about the Company’s benefit plans/programs.

Equal Opportunity at Sentry

Sentry is committed to providing equal employment opportunities to its employees and candidates for employment regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, or other legally-protected characteristic. This commitment includes the provision of reasonable accommodations to employees and candidates for employment with physical or mental disabilities who require such accommodations in order to (a) perform the essential functions of their jobs, or (b) seek employment with Sentry. We strive to build a diverse team, with an inclusive culture where every teammate can thrive. Sentry is an open-source company because we believe that everyone, everywhere, should have the ability and tools to make great software. Software should be accessible. That starts with making our industry accessible.

If you need assistance or an accommodation due to a disability, you may contact us at accommodations@sentry.io.

Want to learn more about how Sentry handles applicant data? Get the details in our Applicant Privacy Policy.

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More about this job

Responsibilities

You will act as a technical lead for agentic operations, performing deep-dive debugging and root-cause analysis on complex issues. Additionally, you will engineer autonomous support paths and build context into systems to resolve high-impact architectural puzzles.

Requirements

Candidates must have 5-8+ years of experience in technical support, systems engineering, or software development with mastery of Python, JavaScript, Java, or Ruby. Strong knowledge of distributed systems, APIs, and AI/LLM orchestration is required to succeed in this role.

Skills

Technical support engineering
Systems engineering
Software development
Python
JavaScript
Java
Ruby
Distributed systems
Microservices
APIs
LLM orchestration
RAG
Debugging
Root-cause analysis
Distributed tracing
Agentic operations

Benefits

Incentive compensation
Equity grants
Paid time off
Group health insurance coverage

Visa sponsorship

Not detected in the job text

Keywords

Technical Support
Systems Engineering
Software Development
SaaS
Python
JavaScript
Java
Ruby
Distributed Systems
Microservices
APIs
LLM
RAG
Debugging
Observability
SDK
Agentic Ops
MCP
GitHub
Discord
CI/CD
Automation
Architecture
Root-cause analysis
Developer Advocate

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